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Ni‐Catalyzed Deacylative Oxosulfonamidation of Vinyl Acetate

Ni‐Catalyzed Deacylative Oxosulfonamidation of Vinyl Acetate A simple and efficient method for the synthesis of benzoxazolidines from the reaction of sulfonamidoalcohol and vinyl acetate was reported. The Ni‐catalyzed deacylation of vinyl acetate results in O‐alkenylated intermediate, which subsequently undergoes intramolecular annulation to afford C2‐alkylated benzoxazolidines. Scope of this method was also extended for the synthesis of other heterocycles of this class such as oxazolidine, benzoxazinolidine and benzimidazolidine. Halofunctionalization was also performed in‐situ in a sequential fashion in the presence of a halogen source. Most importantly, this reaction operates under ligand‐free conditions by using a bench‐top catalyst and does not require any inert atmosphere or dry solvent or any expensive terminal oxidant. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Ni‐Catalyzed Deacylative Oxosulfonamidation of Vinyl Acetate

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References (51)

Publisher
Wiley
Copyright
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201900008
Publisher site
See Article on Publisher Site

Abstract

A simple and efficient method for the synthesis of benzoxazolidines from the reaction of sulfonamidoalcohol and vinyl acetate was reported. The Ni‐catalyzed deacylation of vinyl acetate results in O‐alkenylated intermediate, which subsequently undergoes intramolecular annulation to afford C2‐alkylated benzoxazolidines. Scope of this method was also extended for the synthesis of other heterocycles of this class such as oxazolidine, benzoxazinolidine and benzimidazolidine. Halofunctionalization was also performed in‐situ in a sequential fashion in the presence of a halogen source. Most importantly, this reaction operates under ligand‐free conditions by using a bench‐top catalyst and does not require any inert atmosphere or dry solvent or any expensive terminal oxidant.

Journal

Asian Journal of Organic ChemistryWiley

Published: Feb 1, 2019

Keywords: ; ; ; ;

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